Chalcogen Bonded Directly To The Hetero Ring Patents (Class 549/475)
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Patent number: 6051723Abstract: The present invention relates to new 3-aryl-4-hydroxy-.DELTA..sup.3 -dihydrofuranone derivatives of the formula (I) ##STR1## in which A and B together with the carbon atom to which they are bonded form an unsubstituted or substituted 5- to 7-membered ring which is interrupted by at least one hetero atom,X represents alkyl, halogen or alkoxy,Y represents hydrogen, alkyl, halogen, alkoxy or halogenoalkyl,Z represents alkyl, halogen or alkoxy,n represents a number 0, 1, 2 or 3,G represents hydrogen (a) or one of the groups ##STR2## E represents a metal ion equivalent or an ammonium ion, L represents oxygen or sulphur,M represents oxygen or sulphur andR.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 have the meanings given in the description, to processes for their preparation, and to their use as pesticides.Type: GrantFiled: August 13, 1998Date of Patent: April 18, 2000Assignee: Bayer AktiengesellschaftInventors: Reiner Fischer, Thomas Bretschneider, Gunther Beck, Hermann Hagemann, Christoph Erdelen, Ulrike Wachendorff-Neumann, Wolfram Andersch, Norbert Mencke, Andreas Turberg
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Patent number: 6040444Abstract: Disclosed are processes for preparing furan nitrone compounds using a furan carbonyl compound and a hydroxylamine compound.Type: GrantFiled: May 24, 1999Date of Patent: March 21, 2000Assignee: Centaur Pharmaceuticals, Inc.Inventors: Allan L. Wilcox, Yong-Kang Zhang
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Patent number: 6040328Abstract: The objects of the present invention are:novel organoselenium compounds: aromatic diselenides and selenosulphides;the use of said novel compounds as antioxidant agents;pharmaceutical compositions containing them;a method of preparation of said novel compounds.Type: GrantFiled: August 31, 1999Date of Patent: March 21, 2000Assignee: Oxis International S.A.Inventors: Catherine Tailhan-Lomont, Irene Erdelmeier, Marc Moutet, Jean Chaudiere, Jean-Claude Yadan
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Patent number: 6025519Abstract: Cyclobutane-1,2-dicarboxylic esters of the formula: ##STR1## in which R.sup.1 is a C.sub.1-8 -alkyl group, an optionally substituted mono- or bicyclic cycloaliphatic group having 3 to 10 ring carbon atoms, an optionally substituted aryl or arylalkyl group or an optionally substituted saturated heterocyclic group and R.sup.2 is either C.sub.1-4 -alkyl or both radicals R.sup.2 together form a group of the formula --(CH.sub.2).sub.n --(n is 2 to 4), are prepared from the corresponding maleic or fumaric esters and ketene acetals in the presence of a Lewis acid and a sterically hindered base. The reaction is stereoselective when optically active maleic or fumaric esters are employed. The cyclobutane-1,2-dicarboxylic esters (I), in particular those having trans configuration, are intermediates in the synthesis of pharmaceutically active compounds.Type: GrantFiled: July 20, 1998Date of Patent: February 15, 2000Assignee: Lonza, Ltd.Inventor: Andreas Brunner
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Patent number: 6025392Abstract: Substituted tetrahydrofuran analogs of F-series prostaglandins and methods of their use in treating glaucoma and ocular hypertension are disclosed.Type: GrantFiled: July 2, 1998Date of Patent: February 15, 2000Assignee: Alcon Laboratories, Inc.Inventors: Robert D. Selliah, Mark R. Hellberg, Peter G. Klimko, Verney L. Sallee, Paul W. Zinke
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Patent number: 6020343Abstract: The invention encompasses the novel compound of Formula I useful in the treatment of cyclooxygenase-2 mediated diseases. ##STR1## The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of Formula I.Type: GrantFiled: June 15, 1998Date of Patent: February 1, 2000Assignee: Merck Frosst Canada, Inc.Inventors: Michel Belley, Jacques Yves Gauthier, Erich Grimm, Yves LeBlanc, Chun-Sing Li, Michel Therien, Cameron Black, Petpiboon Prasit, Cheuk-Kun Lau, Patrick Roy
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Patent number: 6013812Abstract: The present invention relates to a process for the production of five-membered or six-membered cyclic ethers, in particular of anhydropolyols, by acid-catalysed cyclodehydration of polyols that contain at least two hydroxyl groups with a spacing enabling ring formation--that is to say, preferably with a spacing of 4 or 5 C atoms. The invention is directed in particular towards the production of anhydrotetritols, anhydropentitols and, particularly preferred, anhydrohexitols, from tetritols, pentitols and hexitols, respectively.Type: GrantFiled: October 30, 1998Date of Patent: January 11, 2000Assignee: Degussa AktiengesellschaftInventors: Thomas Haas, Olaf Burkhardt, Marcus Morawietz, Rudolf Vanheertum, Agnes Bourrel
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Patent number: 6013813Abstract: The present invention deals with the composition of matter and the utilization of certain novel sorbitol guerbet esters which are prepared by the reaction of a guerbet acid and a sorbitol as emulsifiers.Type: GrantFiled: August 24, 1998Date of Patent: January 11, 2000Assignee: Hansotech IncInventor: Anthony J. O'Lenick, Jr.
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Patent number: 6005113Abstract: The invention relates to fluorescent dyes that are substituted or unsubstituted derivatives of 1-(isoindolyl)methylene-isoindole that are bound through both isoindole nitrogens to a boron difluoride moiety, forming a fluorescent dibenzopyrrometheneboron difluoride compound ##STR1## that is further substituted by bathochromic substituents that are aryl or heteroaryl moieties further substituted by an additional aryl or heteroaryl, that is itself optionally further substituted by an additional aryl or heteroaryl. These aryl and heteroaryl groups are separated by a covalent bond, or by an ethenyl, butadienyl or hexatrienyl linkage. The dyes of the invention are particularly useful as labels for carriers, particularly polymeric microparticles. The resulting microparticles have a long-wavelength fluorescence emission, and possess utility for tracing flow in biological systems, particularly in tracing blood flow.Type: GrantFiled: May 14, 1997Date of Patent: December 21, 1999Assignee: Molecular Probes, Inc.Inventors: Yexin Wu, Dieter H. Klaubert, Hee Chol Kang, Yu-Zhong Zhang
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Patent number: 6004957Abstract: The present invention relates to a novel class of sulfonamides which are aspartyl protease inhibitors. In one embodiment, this invention relates to a novel class of HIV aspartyl protease inhibitors characterized by specific structural and physicochemical features. This invention also relates to pharmaceutical compositions comprising these compounds. The compounds and pharmaceutical compositions of this invention are particularly well suited for inhibiting HIV-1 and HIV-2 protease activity and consequently, may be advantageously used as anti-viral agents against the HIV-1 and HIV-2 viruses. This invention also relates to methods for inhibiting the activity of HIV aspartyl protease using the compounds of this invention and methods for screening compounds for anti-HIV activity.Type: GrantFiled: July 22, 1998Date of Patent: December 21, 1999Assignee: Vertex Pharmaceuticals, IncorporatedInventors: Roger D. Tung, Mark A. Murcko, Govinda R. Bhisetti
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Patent number: 5994397Abstract: Substituted tetrahydrofuran analogs of prostagladins and methods of their use in treating glaucoma and ocular hypertension are disclosed.Type: GrantFiled: April 4, 1997Date of Patent: November 30, 1999Assignee: Alcon Laboratories, Inc.Inventors: Robert D. Selliah, Peter G. Klimko
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Patent number: 5986110Abstract: The invention relates to a heterogeneous vanadium-phosphorus oxide catalyst system for the selective oxidation of hydrocarbons, which may or may not be saturated, comprising a support based on one or more metal oxides, and vanadium-phosphorus oxide in an amount of from 0.01 to 45 wt. %, based on the weight of the catalyst and calculated as (VO).sub.2 P.sub.2 O.sub.7, to a process for the selective oxidation of an organic compound in the presence of a vanadium-phosphorus oxide catalyst, which process comprises an oxidation and a reduction phase, wherein a hydrocarbon is contacted with said catalyst in the reduction phase and in oxidized or non-oxidized form is adsorbed to the catalyst, whereafter the thus loaded catalyst is brought into the oxidation phase, the desired product is formed in the presence of gaseous oxygen and subsequently separated.Type: GrantFiled: March 26, 1997Date of Patent: November 16, 1999Assignee: Engelhard De Meern B. V.Inventors: John Wilhelm Geus, Rudolf Alfred Overbeck
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Patent number: 5955496Abstract: The present invention provides novel biologically active tetrahydrofuran diols of arachidonic acid.Type: GrantFiled: August 12, 1997Date of Patent: September 21, 1999Assignee: The Regents of the University of CaliforniaInventors: Bruce D. Hammock, Mehran F. Moghaddam, Jeffrey M. Cheek, Babak Borhan, James Fergusson, David F. Grant, Jessica F. Greene, Kazuhiko Matoba, Jiang Zheng, Marlene F. Sisemore
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Patent number: 5942507Abstract: Disclosed are furan nitrone compounds and pharmaceutical compositions containing such compounds. The disclosed compounds are useful as analytical reagents for detecting free radicals and as therapeutics for treating a wide variety of medical dysfunctions and diseases.Type: GrantFiled: July 17, 1997Date of Patent: August 24, 1999Assignee: Centaur Pharmaceuticals, Inc.Inventors: Judith A. Kelleher, Kirk R. Maples, Lowell David Waterbury, Allan L. Wilcox, Hong Xu, Yong-Kang Zhang
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Patent number: 5935993Abstract: The present invention relates to molecules capable of modulating tyrosine signal transduction to prevent and treat cell proliferative disorders or cell differentiation disorders associated with particular tyrosine kinases by inhibiting one or more abnormal tyrosine kinase activities.Type: GrantFiled: October 24, 1997Date of Patent: August 10, 1999Assignee: Sugen, Inc.Inventors: Peng Cho Tang, Li Sun, Asaad S. Nematalla, Gerald McMahon
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Patent number: 5932731Abstract: The present invention provides a process for preparing an aromatic or heteroaromatic thiol represented by the formula (2), the process comprising hydrolyzing an aromatic or heteroaromatic halogenated methyl sulfide represented by the formula (1)Ar.paren open-st.SCH.sub.3-m X.sub.m).sub.n (1)Ar.paren open-st.SH).sub.n (2)wherein Ar is an aromatic or heteroaromatic ring which has no substituent or which has an optional substituent or substituents, X is a halogen atom, m is an integer of 1 to 3 and n is 1 or 2.Type: GrantFiled: December 22, 1997Date of Patent: August 3, 1999Assignee: Sumitomo Seika Chemicals Co., Ltd.Inventors: Hiroshi Goda, Mikio Yamamoto, Jun-ichi Sakamoto, Hitoshi Karino
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Patent number: 5928515Abstract: The chiral isomers of 3-hydroxytetrahyrofuran are separated by means of liquid chromatography using a stationary phase comprising a substituted polysaccharide carbamate. The separation may be performed using a simulated moving bed adsorbent system. Suitable mobile phase materials comprise a mixture of a light paraffin and a low molecular weight aliphatic alcohol such as a mixture of n-hexane and ethanol. Amylose is the preferred polysaccharide.Type: GrantFiled: December 12, 1997Date of Patent: July 27, 1999Assignee: UOP LLCInventors: Beth McCulloch, Peter K. Nickl
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Patent number: 5919965Abstract: A phosphorus ester oligomer having the structure: ##STR1## wherein A can be the same or different in each monomeric unit and each is independently selected from the group consisting of oxygen, sulfur, lower alkyl, alkyl- or aryl-substituted amino and aminoalkyl; B.sub.1 and B.sub.2 can be the same or different and each is independently selected from hydrogen, lower alkyl, a labelling group, a protecting group, a phosphoramidate or a phosphomonoester; R.sub.1 can be the same or different in each monomeric unit, and in at least one of the non-nucleotide monomeric units, R.sub.Type: GrantFiled: January 18, 1995Date of Patent: July 6, 1999Assignee: Genzyme CorporationInventors: Robert Gerard Gentles, Alan F. Cook, Morris Jonathan Rudolph, Reza Fathi
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Patent number: 5912248Abstract: Compounds of the formula ##STR1## in which X represents a bond, S, SO or SO.sub.2 ; and R is as defined in the specification are useful as modulators of metabotropic glutamate receptor function.Type: GrantFiled: November 14, 1996Date of Patent: June 15, 1999Assignee: Eli Lilly and CompanyInventors: Carmen Dominguez Fernandez, James Allen Monn, Matthew John Valli
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Patent number: 5902887Abstract: Compounds formed by reacting a protected amino acid with an alkali metal enolate of an alkyl acetate are reacted with a halogenating agent for halogenation of the 2-position, or a protected amino acid is reacted with an alkali metal enolate of an alkyl halogenoacetate, to form a 4-amino-3-oxo-2-halogenobutanoic acid ester derivative, and hydrolysis and decarboxylation are conducted to produce a 3-amino-2-oxo-1-halogenopropane derivative or its salt. The present method is a useful process for producing a 3-amino-2-oxo-1-halogenopropane derivatives which can easily be converted to a 3-amino-1,2-epoxypropane.Type: GrantFiled: April 14, 1998Date of Patent: May 11, 1999Assignee: Ajinomoto Co., Inc.Inventors: Yutaka Honda, Satoshi Katayama, Kunisuke Izawa, Masakazu Nakazawa, Takayuki Suzuki, Naoko Kanno
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Patent number: 5886167Abstract: 2'-Deoxy-2'-fluorocoformycin and 2'-deoxy-8-epi-2'-fluorocoformycin are synthesized in this invention through a multi-stage process via 3,5-di-O-benzoyl-2-deoxy-2-fluoro-.alpha.- and -.beta.-D-ribofuranosyl bromides. Further, according to this invention, 2'-deoxy-2'-epi-2'-fluorocoformycin and 2'-deoxy-8,2'-diepi-2'-fluorocoformycin are synthesized by a multi-stage process starting from 3,5-di-O-benzoyl-2-deoxy-2-fluoro-.alpha.-D-arabinofuranosyl bromide. These four 2'-fluoro derivatives of coformycin are novel compounds and have high enzyme-inhibitory activities against adenosine deaminase. In particular, these novel compounds are useful substances which exhibit therapeutic effects on acute lymphocytic leukemias due to their high enzyme-inhibitory activities above-mentioned. In addition, a variety of intermediates are obtained as novel compounds which are useful for the synthesis of the aforesaid novel 2'-fluoro derivatives of coformycin.Type: GrantFiled: December 15, 1997Date of Patent: March 23, 1999Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu KaiInventors: Tomio Takeuchi, Sumio Umezawa, Tsutomu Tsuchiya, Yoshiaki Takahashi
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Patent number: 5883106Abstract: Novel compounds having the ability to inhibit 5-lipoxygenase enzyme and having the following formula I: ##STR1## and the pharmaceutically acceptable salts thereof, wherein Ar.sup.1 is a heterocyclic moiety which is selected from imidazolyl, pyrrolyl, pyrazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, indolyl, indazolyl and benzimidazolyl, which is bonded to X.sup.1 through a ring nitrogen atom, and which may be optionally substituted with one or two substituents selected from halo, hydroxy, cyano, amino, and C.sub.1-4 alkyl; X.sup.1 is a direct bond or C.sub.1-4 alkylene; Ar.sup.2 is phenylene optionally substituted with halo, hydroxy, cyano, and amino X.sup.2 is --A--X-- or --X--A-- wherein A is a direct bond or C.sub.1-4 alkylene and X is oxy, thio, sulfinyl or sulfonyl; Ar.sup.3 is phenylene, pyridylene, thienylene, furylene, oxazolylene or thiazolylene optionally substituted with one or two substituents selected from halo, hydroxy, cyano, amino and C.sub.1-4 alkyl; R.sup.1 and R.sup.2 are each C.sub.Type: GrantFiled: February 6, 1998Date of Patent: March 16, 1999Assignee: Pfizer Inc.Inventors: Rodney W. Stevens, Takashi Mano, Kazunari Nakao, Yoshiyuki Okumura
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Patent number: 5874472Abstract: Compounds of formula (I) and salts, esters and amides thereof, wherein R.sup.1 is a C.sub.1-6 straight or branched chain alkyl group, a C.sub.3-6 cycloalkyl group, a thiol group optionally substituted by a C.sub.1-6 alkyl group, or an amino group optionally substituted by one or two alkyl or alkenyl groups; R.sup.2 is H, C.sub.1-7 straight or branched chain alkyl, C.sub.3-6 cycloalkyl, C.sub.2-7 alkenyl or benzyl; A is a 5 or 6 membered aromatic carbocyclic or heterocyclic ring which may optionally be substituted by one or more suitable substituents such as C.sub.1-6 alkyl, C.sub.1-6 alkoxy, hydroxy, halo, nitro, cyano, trifluoro C.sub.1-6 alkyl, amino, C.sub.1-6 alkylamino or di C.sub.1-6 alkylamino; r is 0, 1 or 2; their use in medicine and in particular for conditions requiring inhibition of the NO Synthase enzyme, pharmaceutical formulations and processes for the preparation thereof are disclosed.Type: GrantFiled: March 18, 1996Date of Patent: February 23, 1999Assignee: Glaxo Wellcome Inc.Inventors: Barry George Shearer, Karl Witold Franzmann, Harold Francis Hodson
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Patent number: 5866602Abstract: Keto-substituted tetrahydrofuran analogs of prostaglandins and methods of their use in treating glaucoma and ocular hypertension are disclosed.Type: GrantFiled: June 18, 1997Date of Patent: February 2, 1999Assignee: Alcon Laboratories, Inc.Inventor: Robert D. Selliah
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Patent number: 5856323Abstract: 2,5-Diaryl tetrahydrofurans, 2,5-diaryl tetrahydrothiophenes, 2,4-diaryl tetrahydrofurans, 2,4-diaryl tetrahydrothiophenes, 1,3-diaryl cyclopentanes, 2,4-diaryl pyrrolidines, and 2,5-diaryl pyrrolidines are disclosed that reduce the chemotaxis and respiratory burst leading to the formation of damaging oxygen radicals of polymorphonuclear leukocytes during an inflammatory or immune response. The compounds exhibit this biological activity by acting as PAF receptor antagonists, by inhibiting the enzyme 5-lipoxygenase, or by exhibiting dual activity, i. e., by acting as both a PAF receptor antagonist and inhibitor of 5-lipoxygenase.A method to treat disorders mediated by PAF or leukotrienes is also disclosed, that includes administering an effective amount of one or more of the above-identified compounds or a pharmaceutically acceptable salt thereof, optionally in a pharmaceutically acceptable carrier.Type: GrantFiled: June 7, 1995Date of Patent: January 5, 1999Assignee: CytoMed, Inc.Inventors: Xiong Cai, Sajjat Hussoin, San-Bao Hwang, David Killian, T. Y. Shen
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Patent number: 5856353Abstract: The present invention relates to a novel class of sulfonamides which are aspartyl protease inhibitors. In one embodiment, this invention relates to a novel class of HIV aspartyl protease inhibitors characterized by specific structural and physicochemical features. This invention also relates to pharmaceutical compositions comprising these compounds. The compounds and pharmaceutical compositions of this invention are particularly well suited for inhibiting HIV-1 and HIV-2 protease activity and consequently, may be advantageously used as anti-viral agents against the HIV-1 and HIV-2 viruses. This invention also relates to methods for inhibiting the activity of HIV aspartyl protease using the compounds of this invention and methods for screening compounds for anti-HIV activity.Type: GrantFiled: June 7, 1995Date of Patent: January 5, 1999Assignee: Vertex Pharmaceuticals, IncorporatedInventors: Roger D. Tung, Mark A. Murcko, Govinda R. Bhisetti
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Patent number: 5856573Abstract: A process for producing a compound of the formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and are hydrogen or alkyl, and R is hydrogen or alkyl, which comprises removing the protective group (P) of hydroxyl of a compound of the formula (II): ##STR2## wherein P is a protective group of hydroxyl, .about. indicates an E-isomer, Z-isomer or a mixture thereof, and the other symbols are as defined above; and an intermediate for the production of the compound of the formula (I).Type: GrantFiled: June 10, 1997Date of Patent: January 5, 1999Assignee: Shionogi & Co., LtdInventors: Akira Takase, Hiroyuki Kai, Takami Murashi
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Patent number: 5814660Abstract: Substituted tetrahydrofuran analogs of prostaglandins and methods of their use in treating glaucoma and ocular hypertension are disclosed.Type: GrantFiled: June 18, 1997Date of Patent: September 29, 1998Assignee: Alcon Laboratories, Inc.Inventor: Robert D. Selliah
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Patent number: 5811593Abstract: The present invention is for a process for preparing monoacetals of hydroquinone wherein said process provides for higher yields of greater purity. Said process utilizes a two step reaction wherein a protected hydroquinone is reacted with an enol ether to form a protected intermediate. Upon hydrogenolysis of said intermediate a final product, monoacetal hydroquinone, is formed having higher degree of purity and in greater yields that the yields attributed to reactions known in the art.Type: GrantFiled: November 12, 1996Date of Patent: September 22, 1998Assignee: The Procter & Gamble CompanyInventors: John David Carter, Jack Lee Parsons, David Fred Starks
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Patent number: 5789394Abstract: Nucleotide analogues having the general formula (I) and pharmaceutically acceptable derivatives: ##STR1## wherein n is 0 or an integer; X is O or S, CH.sub.2, CH-halogen, CH--N.sub.3, or C.dbd.CH.sub.2 ;Q and U are independently selected from: O, S, and CH(R.sub.a) wherein R.sub.a is hydrogen, OH, halogen, N.sub.3, NH.sub.2, SH, carboxyl, C.sub.1-6 alkyl or R.sub.a is CH.sub.2 (R.sub.b) wherein R.sub.b is hydrogen, OH, SH, NH.sub.2, C.sub.1-6 alkyl or carboxyl; or both Q and U are CH when Q and U are linked by a double bond;Z is selected from: O, a C.sub.1-6 alkoxy, a C.sub.1-6 thioalkyl, a C.sub.1-6 aminoalkyl, (CH.sub.2).sub.m wherein m is 0 or an integer, and N(R.sub.c).sub.2 wherein both R.sub.c are independently hydrogen or a C.sub.1-6, alkyl; andR2 is a purine or pyrimidine base or an analogue or derivative thereof are disclosed. Members of this series of analogues possess anti-viral activity.Type: GrantFiled: April 29, 1996Date of Patent: August 4, 1998Inventors: Nghe Nguyen-Ba, Miguel Quimpere, Laval Chan Chung Kong, William L. Brown, Gervais Dionne
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Patent number: 5783701Abstract: The present invention relates to a novel class of sulfonamides which are aspartyl protease inhibitors. In one embodiment, this invention relates to a novel class of HIV aspartyl protease inhibitors characterized by specific structural and physicochemical features. This invention also relates to pharmaceutical compositions comprising these compounds. The compounds and pharmaceutical compositions of this invention are particularly well suited for inhibiting HIV-1 and HIV-2 protease activity and consequently, may be advantageously used as anti-viral agents against the HIV-1 and HIV-2 viruses. This invention also relates to methods for inhibiting the activity of HIV aspartyl protease using the compounds of this invention and methods for screening compounds for anti-HIV activity.Type: GrantFiled: February 23, 1995Date of Patent: July 21, 1998Assignee: Vertex Pharmaceuticals, IncorporatedInventors: Roger D. Tung, Mark A. Murcko, Govinda Rao Bhisetti
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Patent number: 5780649Abstract: A process for preparing optically active 3-hydroxy-.gamma.-butyrolactone or optically active 3-hydroxytetrahydrofuran through a short route and by using an easily available and inexpensive starting material and an inexpensive reagent easy to handle is disclosed. The process comprises cyclizing an optically active compound represented by formula (II): ##STR1## wherein Q represents an alkoxycarbonyl group having 1 to 4 carbon atoms or a hydroxymethyl group; X represents a halogen atom; and the asterisk * means an asymmetric carbon atom, under an acidic condition.Type: GrantFiled: September 4, 1996Date of Patent: July 14, 1998Assignee: Takasago International CorporationInventors: Yoshifumi Yuasa, Masao Konno, Noboru Sano
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Patent number: 5773607Abstract: 2'-Deoxy-2'-fluorocoformycin and 2'-deoxy-8-epi-2'-fluorocoformycin are synthesized in this invention through a multi-stage process via 3,5-di-O-benzoyl-2-deoxy-2-fluoro-.alpha.- and -.beta.-D-ribofuranosyl bromides. Further, according to this invention, 2'-deoxy-2'-epi-2'-fluorocoformycin and 2'-deoxy-8,2'-diepi-2'-fluorocoformycin are synthesized by a multi-stage process starting from 3,5-di-O-benzoyl-2-deoxy-2-fluoro-.alpha.-D-arabinofuranosyl bromide. These four 2'-fluoro derivatives of coformycin are novel compounds and have high enzyme-inhibitory activities against adenosine deaminase. In particular, these novel compounds are useful substances which exhibit therapeutic effects on acute lymphocytic leukemias due to their high enzyme-inhibitory activities above-mentioned. In addition, a variety of intermediates are obtained as novel compounds which are useful for the synthesis of the aforesaid novel 2'-fluoro derivatives of coformycin.Type: GrantFiled: March 22, 1996Date of Patent: June 30, 1998Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu KaiInventors: Tomio Takeuchi, Sumio Umezawa, Tsutomu Tsuchiya, Yoshiaki Takahashi
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Patent number: 5763688Abstract: The present invention provides a method for producing a alcohol including an optically active alcohol by hydrogenating a carbonyl compound in the presence of a homogeneous catalyst, a base and a nitrogen-containing organic compound. Thus, the reaction employs an inexpensive catalyst and proceeds in high yield and high efficiency.Type: GrantFiled: December 7, 1995Date of Patent: June 9, 1998Assignee: Research Development Corporation of JapanInventors: Takao Ikariya, Takeshi Ohkuma, Hirohito Ooka, Shohei Hashiguchi, Nobuo Seido, Ryoji Noyori
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Patent number: 5750735Abstract: Carbapenem antibiotic compounds of the general formula: ##STR1## wherein the moiety ##STR2## is a 4, 5 or 6 membered mono, di- or tri-substituted oxygen or sulfur containing ring; wherein Z is oxygen, sulfur, sulfoxide and sulfone, pharmaceutical compositions thereof useful for the treatment of bacterial infections, processes for preparing the compounds and new intermediates useful in the process.Type: GrantFiled: May 19, 1995Date of Patent: May 12, 1998Assignee: American Cyanamid CompanyInventors: Yang-I Lin, Panayota Bitha, Subas Sakya, Timothy W. Strohmeyer, Karen Bush, Carl Bernard Ziegler, Gregg Brian Feigelson
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Patent number: 5744574Abstract: Isomaleimides and polyisomaleimides can be prepared by a method comprising the steps in sequence: admixing a maleamic acid or polymaleamic acid with an acid halide, reacting the admixture with a tertiary amine at a temperature sufficiently low to suppress the formation of a maleimide, and isolating the resulting isomaleimide or polyisomaleimide. Polymerization of a polyisomaleimide with a polynucleophilic monomer (polythiol, polyol, polyamine) produces novel polymers.Type: GrantFiled: December 5, 1995Date of Patent: April 28, 1998Assignee: Minnesota Mining and Manufacturing CompanyInventors: Stephen A. Ezzell, Richard G. Hansen, Gregory J. Anderson
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Patent number: 5693832Abstract: A process for the hydroformylation of allyl alcohol is disclosed, which comprises reacting allyl alcohol with carbon monoxide and hydrogen in the presence of a rhodium compound and a diphosphine compound represented by formula (I) or (II) ##STR1## wherein R.sup.1 represents an alkyl group or a substituted or unsubstituted aryl group; and R.sup.2 and R.sup.3 each represents an alkyl group or a hydrogen atom.Type: GrantFiled: June 27, 1994Date of Patent: December 2, 1997Assignee: Showa Denko K.KInventors: Tetsuro Fujita, Kenichiro Maki, Kuniomi Marumo
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Patent number: 5693667Abstract: A compound, composition, and method for controlling Take-all disease of plants by applying a fungicide of the formula: ##STR1## wherein Z.sub.1 and Z.sub.2 are carbons of a furan ring; A is selected from the group consisting of --C(X)-amine wherein the amine is substituted with a first and a second amine substituent or with an alkylaminocarbonyl and a hydrogen, --C(O)--SR.sub.3 ; --NH--C(X)R.sub.4, and --C(.dbd.NR.sub.3)--XR.sub.7 ;B is --W.sub.m --Q(R.sub.2).sub.3 or selected from o-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R.sub.4 ; Q is C, Si, Ge, or Sn; W is --C(R.sub.3).sub.p H.sub.(2-p) --; or when Q is C, W may also be selected from --N(R.sub.3).sub.m H.sub.(1-m) --, --S(O).sub.p --, and --O--; X is O or S; n is 0, 1, or 2; m is 0 or 1; p is 0, 1, or 2;wherein two R.sub.Type: GrantFiled: December 28, 1994Date of Patent: December 2, 1997Assignee: Monsanto CompanyInventors: Dennis Paul Phillion, Diane Susan Braccolino, Matthew James Graneto, Wendell Gary Phillips, Karey Alan Van Sant, Daniel Mark Walker, Sai Chi Wong
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Patent number: 5691372Abstract: The present invention relates to a novel class of sulfonamides which are aspartyl protease inhibitors. This invention also relates to pharmaceutical compositions comprising these compounds. The compounds and pharmaceutical compositions of this invention are particularly well suited for inhibiting HIV-1 and HIV-2 protease activity and consequently, may be advantageously used as anti-viral agents against the HIV-1 and HIV-2 viruses. This invention also relates to methods for inhibiting the activity of HIV aspartyl protease using the compounds of this invention.Type: GrantFiled: April 19, 1995Date of Patent: November 25, 1997Assignee: Vertex Pharmaceuticals IncorporatedInventors: Roger D. Tung, Govinda Rao Bhisetti
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Patent number: 5684166Abstract: Compounds having utility in medicine in countering cellular malfunction e.g. in conditions embraced by the general term "cancer", which compounds normally exist us a keto-enol tautomeric pair, the racetalc keto form of which is rapresented by formula (Ia), wherein R is a hydrogen, lower alkyl, acyl, or another functional group of up to 6 carbons including at least one hetero atom, which atom may be directly bonded to the .beta.-carbon, which compound may be in the acylic form shown or in a cyclic form as equilibrium keto-enol tautomer derivatives and anomeric forms thereof, including enantiomers when R is hydrogen and diastereoisomers when R is another group.Type: GrantFiled: April 4, 1996Date of Patent: November 4, 1997Assignee: Biocure LimitedInventor: Neil Geddes Clarkson Hendry
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Patent number: 5684198Abstract: Amides having formula I: ##STR1## wherein E, X, R.sup.2 and R.sup.3 have the meanings given in the specification, and pharmaceutically acceptable salts and pharmaceutically acceptable in vivo hydrolysable esters thereof,which are useful in the treatment of urinary incontinence. Further provided are processes for preparing the aides and pharmaceutical compositions containing them.Type: GrantFiled: August 23, 1996Date of Patent: November 4, 1997Assignee: Imperial Chemical Industries, PLCInventors: Keith Russell, Cyrus John Ohnmacht, Keith Hopkinson Gibson
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Patent number: 5684167Abstract: 2-Hydroxy-4-methyltetrahydrofuran is prepared by reacting 2-methyl-2-propen-1-ol with hydrogen and carbon monoxide in the presence of:(a) a rhodium compound, and(b) tris(substituted aryl)phosphite having an electronic parameter (.nu.-value) of 2080 to 2090 cm.sup.-1 and a steric parameter (.theta.-value) of 135.degree. to 190.degree. and having formula (1): ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 independently of each other represent a substituted aryl group having at least 7 carbon atoms, the ratio of said rhodium compound (a) to said tris(substituted aryl) phosphite (b) ranging from 110 to 1000 moles per 1 gram atom of rhodium in said rhodium compound (a).Type: GrantFiled: June 7, 1996Date of Patent: November 4, 1997Assignee: Kuraray Co., Ltd.Inventors: Toshihiro Omatsu, Takashi Onishi, Yasuo Tokitoh
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Patent number: 5672779Abstract: The present invention provides a compound represented by the formula: ##STR1## wherein R.sub.1 denotes a hydrogen atom or a methyl group; R.sub.2 represents a 1-methyl-2-propenyl group, a 1-methyl-2-propynyl group, a 3,3-dihalogeno-1-methyl-2-propenyl group or a C.sub.1 -C.sub.6 alkyl group which may be substituted with at least one halogen atom; and A' represents a hydrogen atom or a protecting group for a hydroxyl group. The compound is useful in the preparation of esters which can be used to control insect pests.Type: GrantFiled: May 1, 1996Date of Patent: September 30, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Tomonori Iwasaki, Masaya Suzuki, Takashi Furukawa, Kazunori Tsushima, Takao Ishiwatari, Toru Tsuchiya
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Patent number: 5665763Abstract: Compounds of the formula ##STR1## wherein: R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined in the specification,Y is alkylene of 3 to 9 carbon atoms,R.sub.5 is alkoxycarbonyl, alkyltetrazolyl, phenyl or a heterocycle chosen from benzoxazolyl, benzathiazolyl, thiadiazolyl, imidazolyl, dihydroimidazolyl, oxazolyl, thiazolyl, oxadiazolyl, pyrazolyl, oxazolinyl, isoxazolyl, isothiazolyl, furyl, triazolyl, thiophenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl or any of the above substituted with alkyl, alkoxyalkyl, cycloalkyl, halo alkyl, hydroxyalkyl, alkoxy, hydroxy, halo, furyl, thienyl, fluoroalkyl;or a pharmaceutically acceptable acid addition salts thereof; N-oxides thereof, are useful as antipirconaviral agents.Type: GrantFiled: August 30, 1996Date of Patent: September 9, 1997Assignee: Sanofi, S.A.Inventors: David J. Aldous, Thomas R. Bailey, Guy Dominic Diana, Theodore J. Nitz
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Patent number: 5663380Abstract: A class of cysteine protease inhibitors which inactivate a cysteine protease by covalently bonding to the protease and releasing a heterocyclic leaving group is presented. The cysteine protease inhibitors of the present invention comprise a first portion which targets a desired cysteine protease and positions the inhibitor near the thiolate anion portion of the active site of the protease, and a second portion which covalently bonds to the cysteine protease and irreversibly deactivates that protease by providing a carbonyl or carbonyl-equivalent which is attacked by the thiolate anion of the active site of the cysteine protease to sequentially cleave a heterocyclic leaving group. The heterocyclic leaving group of the protease inhibitor is of the formula: --O--Het, where Het is a heterocycle having 4-7 atoms in the ring, with at least one of the heterocycle atoms being N, O or S.Type: GrantFiled: January 22, 1996Date of Patent: September 2, 1997Assignee: Prototek, Inc.Inventors: Mary P. Zimmerman, Robert E. Smith
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Patent number: 5653990Abstract: There is provided an ester compound represented by the formula I: ##STR1## wherein R.sub.1 is a methyl group or a hydrogen atom; R.sub.2 is a C.sub.1-6 haloalkyl group; and R.sub.3 is a pyrethroid acid residue, an agent for controlling noxious organisms containing the same as active ingredient and an intermediate for producing the same.Type: GrantFiled: June 21, 1995Date of Patent: August 5, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Tomonori Iwasaki, Kazunori Tsushima, Takashi Furukawa, Takao Ishiwatari, Toru Tsuchiya, Mikako Nakamachi
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Patent number: 5648486Abstract: 2,5-Diaryl tetrahydrofurans, 2,5-diaryl tetrahydrothiophenes, 2,4-diaryl tetrahydrofurans, 2,4-diaryl tetrahydrothiophenes, 1,3-diaryl cyclopentanes, 2,4-diaryl pyrrolidines, and 2,5-diaryl pyrrolidines are disclosed that reduce the chemotaxis and respiratory burst leading to the formation of damaging oxygen radicals of polymorphonuclear leukocytes during an inflammatory or immune response. The compounds exhibit this biological activity by acting as PAF receptor antagonists, by inhibiting the enzyme 5-lipoxygenase, or by exhibiting dual activity, i.e., by acting as both a PAF receptor antagonist and inhibitor of 5-lipoxygenase.A method to treat disorders mediated by PAF or leukotrienes is also disclosed, that includes administering an effective amount of one or more of the above-identified compounds or a pharmaceutically acceptable salt thereof, optionally in a pharmaceutically acceptable carrier.Type: GrantFiled: May 12, 1993Date of Patent: July 15, 1997Assignee: CytoMed, Inc.Inventors: Xiong Cai, Sajjat Hussoin, San-Bao Hwang, David Killian, T. Y. Shen
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Patent number: 5633367Abstract: A process for the preparation of a 2-substituted-3,3-difluorofuran using diethyl ammonium sulfur trifluoride (DAST) and pyridine hydrogen fluoride. The process is particularly useful for producing a 2',2'-difluoronucleoside, particularly 1-(2',2'-difluoro-.beta.-D-arabinofuranosyl)cytosine (also known as 2'-deoxy-2',2'-difluorocytidine), a known antiviral and antitumor agent.Type: GrantFiled: March 24, 1995Date of Patent: May 27, 1997Assignee: Eli Lilly and CompanyInventor: Douglas P. Kjell
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Patent number: 5623081Abstract: Tetrahydrofuanyl compounds of the following formulae: ##STR1## are disclosed.Type: GrantFiled: May 23, 1995Date of Patent: April 22, 1997Inventors: Yang-I Lin, Panayota Bitha, Subas Sakya, Timothy W. Strohmeyer, Karen Bush, Carl B. Ziegler, Gregg B. Feigelson
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Patent number: 5606081Abstract: A process for the preparation of a cyclic ether ketone of the general formula I ##STR1## in which R.sup.1 and R.sup.2 denote hydrogen or C.sub.1 -C.sub.4 alkyl, m and n denote integers from 1 to 5, in which a cyclic ether aldehyde of the general formula I ##STR2## in which have R.sup.1, R.sup.2, m and n have the above meanings, is reacted with an oxygen-containing gas in the presence of a solid or supported catalyst containing copper and/or manganese, at temperatures of from 50.degree. to 300.degree. C. and pressures of from 0.01 to 10 bar.Type: GrantFiled: May 12, 1995Date of Patent: February 25, 1997Assignee: BASF AktiengesellschaftInventors: Werner Schnurr, Rolf Fischer